Justin Bieber’s court cases on both sides of the U.S.-Canadian border might not just lead to more scrutiny by judges and prosecutors, but could also complicate the pop star’s jet-setting ways.

Legal experts said the decision by Toronto authorities to charge Bieber with assault on Wednesday makes the singer’s legal situation more complicated and difficult to untangle. He is already facing a driving under the influence case in Florida, and remains under investigation for felony vandalism in Los Angeles County.

Bieber’s cases are in the early stages and there are no guarantees that the Grammy-nominated singer will be convicted of any charges. But if he is, it will impact how judges view and sentence him, said Stanley L. Friedman, a former federal prosecutor who now practices criminal defense in Los Angeles.

“I think the legal system is much more likely to treat him harshly as somebody who needs to be taught a lesson,” ”Now he’s become a national poster child for being a bad boy.”

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Andrew Flier, a criminal defense attorney who’s represented sports stars and actors, said immigration issues are likely Bieber’s biggest problem at this point. If the singer is convicted in one or both cases, he could receive additional scrutiny when traveling from his homeland, Canada to the United States, where Bieber currently lives.

“Multiple convictions even on misdemeanors could be troublesome to the non-citizen,” Flier said.

Bieber, 19, has pleaded not guilty to DUI, resisting arrest without violence and driving without a valid license in the Miami case. A preliminary toxicology report released Thursday showed that Bieber tested positive for marijuana and the anti-anxiety drug Xanax. The report shows no presence of other illicit drugs in Bieber’s system. Bieber told police after the arrest that he had been smoking marijuana and took a prescription drug.

The singer also remains under investigation for an egg-tossing incident that left his neighbor’s house with thousands of dollars in damage. If Bieber is charged in that case, a California judge may look at the singer more harshly in light of the Florida and Toronto cases, said Stan Goldman, a criminal law professor at Loyola Law School, Los Angeles.

“The fact that you’ve got three is a heck of a lot worse than one,” Goldman said.

Friedman agreed, and said Bieber’s other cases may make it more likely that the singer will be charged in Los Angeles. Prosecutors have a lot of discretion in how they pursue cases, and a judge has limited influence in the early stages about what deal Bieber would be offered or whether the case goes forward.

If Bieber is convicted in any of the cases — which could occur after a trial or potentially a plea deal — he’ll lose the benefit of the doubt that judges often give to first-time offenders, Goldman said.

“These cases could take a while to work out and something’s going to happen first,” he said.

A judge might opt to keep Bieber on a long probation sentence to make sure he stays out of trouble, Goldman said, citing the case of Lindsay Lohan. The actress has been on some form of probation constantly since she took a plea agreement after being arrested twice for driving under the influence and drug possession in 2007.

Numerous stars have had their international travel curtailed because of their legal trouble, and attorneys cited the United States and Canada as both viewing any drug offenses harshly when deciding immigration issues. Japan has blocked the entry of The Rolling Stones over drug convictions and in 1980 deported Paul McCartney for marijuana possession at Narita International Airport. In 2010, Japan blocked Paris Hilton from entering the country just days after she pleaded guilty to a misdemeanor drug charge in Las Vegas.

R&B star Chris Brown must still have his international travel approved by a judge overseeing his probation for his 2009 attack on then-girlfriend Rihanna, and a Los Angeles judge restricted Lohan’s travel during the height of her probation.

David S. Kestenbaum, an attorney who represents a paparazzo charged with driving recklessly to obtain shots of Bieber, said the pop star’s troubles will likely have an impact on his client’s case.

Bieber “has been showing in the last year his character doesn’t have a lot of credibility,” Kestenbaum said.

He agreed with other experts who say Bieber’s chances of being deported from the United States remain low, but he said that doesn’t mean he’ll quickly clear customs if he’s convicted in any of the cases. Agents may scrutinize Bieber and his entourage more, looking for narcotics or other contraband, and some countries may require him to obtain a special visa to enter, Kestenbaum said.